EP0011295A1 - Colorants monoazoiques jaunes de la série des 2-hydroxydibenzofurannes, leur préparation et leur utilisation à la teinture et l'impression de fibres synthétiques hydrophobes - Google Patents

Colorants monoazoiques jaunes de la série des 2-hydroxydibenzofurannes, leur préparation et leur utilisation à la teinture et l'impression de fibres synthétiques hydrophobes Download PDF

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Publication number
EP0011295A1
EP0011295A1 EP79104521A EP79104521A EP0011295A1 EP 0011295 A1 EP0011295 A1 EP 0011295A1 EP 79104521 A EP79104521 A EP 79104521A EP 79104521 A EP79104521 A EP 79104521A EP 0011295 A1 EP0011295 A1 EP 0011295A1
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EP
European Patent Office
Prior art keywords
group
amino
dyes
formula
dyeing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP79104521A
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German (de)
English (en)
Inventor
Ruggero Battisti
Giovanni Bausani
Nicola Mazzaferro
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Montedison SpA
Original Assignee
Montedison SpA
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Filing date
Publication date
Application filed by Montedison SpA filed Critical Montedison SpA
Publication of EP0011295A1 publication Critical patent/EP0011295A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3678—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only oxygen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
    • C09B29/0037—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with two nitrogen atoms

Definitions

  • This invention relates to a new class of water-insoluble yellow monoazo dyes.
  • the present invention relates furthermore to the preparation of the dyes of formula (I) and the use of same.
  • the dyes object of this invention are particularly suitable for dyeing and printing hydrophobic synthetic fibres, in particular polyester fibres, with yellow shades.
  • the dyes of the present invention exhibit a high stability to light, to wet treatments and to heat treatments.
  • the dyes of the present invention have furthermore exhibited an excellent behaviour in the dyeing and printing of polyester-cotton blended fibres, according to known processes used at present, as they have all the main characteristics required for this application, i.e.:
  • the dyes forming the object of this invention are obtained by diazotizing, according to substantially conventional methods, the 1-phenyl-3-amino pyrazols of formula (II) as defined hereinbefore, and by successively coupling, in an acid to basic medium, the diazopyrazols obtained on 2-hydroxy-dibenzofuran of formula (III).
  • the dyes of the present invention can be also prepared by oxidative diazotization of 1-phenyl-3-amino pyrazolins having formula (IV): wherein R , R , X and n have the meanings indicated herein above; in this manner it is possible to obtain the corresponding diazopyrazols, which are then coupled on 2 -hydroxy--dibenzofuran of formula (III), as explained hereinbefore.
  • the abovesaid oxidative diazotation of the pyrazolins of formula (IV) is efficaciously conducted, for example, according to the method forming the object of Italian patent application No. 23725 A/78, according to which the amino-pyrazolins of formula (IV) are treated with nitrous acid in a ratio of from 2:1 to 5:1 in respect of amino-py razolins (IV), in an organic acid medium (acetic or propionic acid) or in an inorganic acid medium (hydrochloric acid, sulphuric acid, etc.) at a temperature in the range of from -10°C to +20°C.
  • the nitrous acid in its turn, is prepared from alkaline or alkyl nitrites, or from nitrosyl-sulphuric acid.
  • 1-phenyl-3-amino pyrazolins (IV) can be prepared by conventional methods.
  • 1-phenyl-3-amino pyrazols (II) can be obtained, in their turn, by oxidizing the corresponding pyrazolins (IV), for example with chloranil in xylene (C. Alberti. Il Farmaco - Ed. Sc. vol. XIX, issue 7, page 638), or by flowing of air through an inert solvent (alcohols, acetic acid, aceto nitrile) in the presence of copper salts (CuCl, CuCl , acetate) at about 20°C-40°C, as described in Belgian patent application No. 855,944 filed by the Applicant.
  • 2-hydroxy-dibenzofuran (III) can be prepared for example from 2-(2'-chlorophenyl)-hydroquinone by heating with NaOH or KOH (US patent No. 2,172,572).
  • the dye obtained after drying was a yellow powder having the following centesimal composition: .
  • the resulting diazo solution was let into 200 g of ice and 100 ml of water, and the nitrous acid in excess was removed by means ⁇ f sulphamic acid.
  • the diazo solution was dropped, at a temperature of from 5° to 10°C, into a solution consisting of 1.84 g (0.01 moles) of 2-hydroxy-dibenzofuran, 100 ml of 36° Be sodium hydrate and 600 ml of water.
  • the yellow dyeing so obtained possessed a high intensity and excellent stabilities to sunlight, to moisture and to thermal treatments.
  • the dried fabric retaining however ah amount of solvent useful to fix the dye, was heat set in warm air at 200°C for 1-2 minutes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
EP79104521A 1978-11-15 1979-11-15 Colorants monoazoiques jaunes de la série des 2-hydroxydibenzofurannes, leur préparation et leur utilisation à la teinture et l'impression de fibres synthétiques hydrophobes Withdrawn EP0011295A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT29817/78A IT1101703B (it) 1978-11-15 1978-11-15 Itcoloranti monoazoici gialli
IT2981778 1978-11-15

Publications (1)

Publication Number Publication Date
EP0011295A1 true EP0011295A1 (fr) 1980-05-28

Family

ID=11228496

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79104521A Withdrawn EP0011295A1 (fr) 1978-11-15 1979-11-15 Colorants monoazoiques jaunes de la série des 2-hydroxydibenzofurannes, leur préparation et leur utilisation à la teinture et l'impression de fibres synthétiques hydrophobes

Country Status (2)

Country Link
EP (1) EP0011295A1 (fr)
IT (1) IT1101703B (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1424732A (fr) * 1964-02-14 1966-01-14 Hoechst Ag Procédé de teinture et impression, notamment de polypropylène contenant du nickel
DE1240601B (de) * 1962-02-28 1967-05-18 Hoechst Ag Verfahren zur Herstellung von metallhaltigen, wasserunloeslichen Azofarbstoffen
GB1531697A (en) * 1976-06-25 1978-11-08 Montedison Spa Pyrazole-azo-pyridone dyes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1240601B (de) * 1962-02-28 1967-05-18 Hoechst Ag Verfahren zur Herstellung von metallhaltigen, wasserunloeslichen Azofarbstoffen
FR1424732A (fr) * 1964-02-14 1966-01-14 Hoechst Ag Procédé de teinture et impression, notamment de polypropylène contenant du nickel
GB1531697A (en) * 1976-06-25 1978-11-08 Montedison Spa Pyrazole-azo-pyridone dyes

Also Published As

Publication number Publication date
IT1101703B (it) 1985-10-07
IT7829817A0 (it) 1978-11-15

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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Inventor name: BATTISTI, RUGGERO

Inventor name: MAZZAFERRO, NICOLA

Inventor name: BAUSANI, GIOVANNI